Glycol esters



Patented Nov. 12, 1940 UNITED STATES PATENT OFFICE Foster Company, a corporation of New Jersey No Drawing. Application April 1, 1937.

\ Serial No. 134,305

3 Claims.

This invention relates to solid to liquid products derived from saturated iatty acids of nondrying animal or vegetable oils and a reactive oxygenated body such as a polyhydric alcohol or 5 a derivative thereof, as will be more fully herein after described.

The non-drying glyceride oils include lard oil, tallow oil, neats-foot oil, palm kernel oil, coconut oil, and the like. The invention will'be'illustrated by examples of products prepared with the aid of coconut oil or its fatty acids. understood, however, that other non-drying oils or their fatty acids such as palm kernel oil or its fatty acids, may replace the coconut oil or its fatty acids.

It will be noted that the oil-acids have as a rule 12 carbon atoms, e. g., lauric acid of coconut oil, or higher, e. g., those of various non-drying oils containing 16 or 18 carbon atoms in the 20 fatty acid component. Stearic and other saturated fatty acids of high carbon content are less desirable for present purposes than the fatty acids of intermediate carbon content. For example, when complexes containing a high or influential proportion of stearic acid are admixed with nitrocellulose in solution there is a tendency to form greasy films which is avoided by using saturated or non-drying oil-acids of lower melting point.

Fatty acids of intermediate carbon content include those saturated acids having more than about 4 carbon atoms and less than stearic acid. Lauric acid has 12 carbon atoms.

The aforesaid reactive oxygenated bodies comprise a wide range of substances of differing chemical and physical properties. The following will serve in an illustrative way:

1. Glycerol, in its various forms-dilute, concentrated, crude or refined.

2. Polyglycerols, or a mixture of polyglycerols 40 and glycerol.

3. Various glycols, such as ethylene or propylene glycol.

These may be derived from petroleum gases, by suitable reaction. Mixtures of glycols sometimes obtained from this source may be used to advantage. The employment of glycols in this Way is referred to in my copending application Serial No. 61,839, filed Oct. 10, 1925, page 1, now Patent'No. 2,072,068.

4. Polyhydric alcohols containing a substituent in the hydroxyl, e. g., mono or dimethyl or propyl ether of glycerol. The mono ethyl ether of ethylene glycol has one hydroxyl free for reactive purposes. The glycerol and the glycol derivatives behave quite differently in the reaction, owing to It should be (onto-410) butylene oxide.

It will be noted that thesereactive oxygenated bodies are chemically different as a class from the non-drying glyceride oils and their fatty acids. Physically also they usually are different, 15 e. g., many are water-soluble or hygroscopic substances.

Example 1' Dlethylene glycol (dihydroxy diethyl monoether) Fatty acids of coconut oil 300 This mixture was heated in an atmosphere of carbon dioxide at 180-210 C. until the resulting ester 25 had an acid number of 19. The ester was a liquid miscible with alcohol, toluol, mineral spirits and linseed oil. It was compatible with nitrocellulose and also with chlorinated rubber.

Example 2 30 Parts by weight Triethylene glycol (dihydroxy triethyl I diether) 40. 3 Fatty acids of coconut oil 35 After heating the above mixture for 6 hours at -210 C. in an atmosphere of carbon dioxide, an amber-colored liquid having an acid number of 12.4 resulted. This ester was miscible with mineral spirits, alcohols, linseed oil and glycol. 40

Example 3 Parts by weight Ethylene glycol 22. 9 Fatty acids of coconut oil 100 45 V This mixture was heated for 6 hours at ISO-210 C. The resulting product was a light-brown solid of softening point 42 C. and acid number 20.5, which was soluble in isopropyl alcohol, toluol, mineral spirits and linseed oil. It was miscible 50 with glycerol, ethylene glycol and diethylene glycol with the range of equal parts or less of the polyhydric alcohol, the resulting solutions being soft masses suitable forsuppository bases, cosmetic creams, textile lubricants and the like. For 55 Parts by weight 20 example, mixed with glycerol in varying proportions compositions of the following softening points were obtained:

Parts by weight Diethylene glycol (dihydroxy diethyl monoether) 13. 3 Laurie acid 50 A light-colored soft solid of softening point 31 C. and acid number 21.4 resulted after the above mixture had been heated at 180-210 C. for 2 hours. This product was readily soluble in solvents such as toluol, butyl acetate, isopropyl alcohol, mineral spirits and linseed oil. Miscibility with mono and diethylene glycol and glycerol occurred when an excess of ester was used. The

following shows the softening point of various mixtures with glycerol.

Glycerol Ester Softening point c. l 2 incompletely miscible 1 3 2s 1 4 29 1 5 31 Example 5 Parts by weight Diethylene glycol ethyl ether 4'! Fatty acids of coconut oil 100 The above mixture was heated at 180210 C. for 5 hours and formed a soft waxy solid of acid number 5.7. This was soluble in the usual lacquer solvents and compatible with nitrocellulose.

The corresponding ester of monoethylene glycol ethyl ether is a liquid.

Example 6 Parts by weight Diethylene glycol 53 Fatty acids of coconut oil 100 These proportions are such as: to form the monoester of the glycol. The mixture was heated at 180-210 C. until the acid number was 18.9. The product was an amber-colored liquid, miscible with nitrocellulose.

The proportions of nitrocellulose in coating compositions may be varied considerably with respect ot the products of the present invention. For very hard surface finish the nitrocellulose may predominate but for softer and more flexible coatings the resin or balsam (as the case may be) can be used in relatively high proportion, say

from 2 to 10 parts by weight to 1 part of nitrocellulose.

The nitrocellulose used may be of low or high viscosity, but preferably I employ a grade slightly over 1 second and not exceeding 5 seconds viscosity in making lacquers, whereas high viscosity nitrocellulose such as Celluloid, cotton or smokeless powder may be employed with the resin or balsam in making molded products, plastic masses for sheeting to form the tread of felt base fioor covering, and for various other purposes.

By employing a non-drying oil fatty acid and especially by reacting the acids of a substantially or relatively saturated glyceride oil such as coconut oil, I reduce the tendency to oxidation changes in a coating on long exposure, and the stabilization thus effected I consider to be of material benefit.

Coconut oil or other animal and vegetable oils embraced herein may be chilled and pressed to secure low cold test grades and either the press cake or the more liquid glycerides employed as a source of the fatty acids. The free fatty acids themselves likewise may be chilled and pressed to secure different grades of varying fluidity.

Generally speaking, I prefer to employ natural glycerides yielding fatty acids which are low in stearic or similar solid fats. In the case of coconut oil, for example, chilling and pressing allow separation into a portion of higher melting point desired in confectionery manufacture, while the more liquid portions may be utilized in making products of the present invention.

In the above examples, therefore, it is understood that cold-test coconut oil or the fatty acids of corresponding titre may be used. The employment of a non-drying substantially oxygenstable cold-test glyceride oil or its fatty acids constitutes one of the specific forms of the invention.

Either the mixed fatty acids may be used or fractions representing relatively pure constituents although the products may differ somewhat. As shown above, the product obtained with the mixed fatty acids of coconut oil differs in consistency from that obtained with lauric acid itself.

For many purposes, especially in making coating compositions, a low acid number is desirable. There is less tendency to livering with basic pigments and in the case of nitrocellulose lacquers a low acid number is considered safer. Also, if the composition is to be used for insulating purposes low acidity is desirable. A complex which has been extensively reacted so that the acid number is 30 or less thus is preferred. To obtain this relatively low index of acidity is one of the requisites of the preferred form of the present invention.

The distilled fatty acids of animal and vegetable oils also may be used in making the nonsiccative complex. Drying or semi-drying oils may be blown to such an extent that they lose siccat'ive properties almost completely. Reactive blown oils or their fatty acids, having substantially non-siccative qualities are included with the raw materials employed in the present invention. These include the blown derivatives of corn, cotton, soya, castor, rape and other vegetable (or animal) oils.

By proceeding in accordance with the foregoacids (as their salts) and the oxygenated body.

such as a polyhydric alcohol, in free state.

This application is a continuation in part of 2. As new compounds, the dlethylene glycol Serial 219,562, filed Sept. 14, 1927, now Patent No. ethyl ether esters of'laurlc acid.

2,089,196. 3. As new compounds, the diethylene glycol What I claim is: ethyl ether esters of the fatty acids of a non-dry- 1. As new compounds,-'- the diethylene glycol ing oil.

ethyl ether esters of the fatty acids having a car- CARLETON ELLIS.

bon content greater than five. 

